新的 8-癸硫基-10-甲硫基嘧啶并[5,4-e][1,2,4]三唑并[1,5-c]嘧啶衍生物的设计、合成和生物活性

IF 1.4 4区 化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR
Huixiang Nie , Linghui He , Anlin Zhao , Haijin Huang , Tao Wang , Jin Luo
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引用次数: 0

摘要

制备了一系列新的 8-癸硫基-10-甲硫基嘧啶并[5,4-e][1,2,4]三唑并[1,5-c]嘧啶衍生物,并通过傅里叶变换红外光谱、1H NMR、13C NMR 和 HRMS 对其进行了表征。生物测定结果表明,当浓度为 500 mg/L 时,标题化合物对蚜虫具有中等至卓越的杀虫活性。其中,8-(癸硫基)-2-((4-氯苯氧基)甲基)-5-丙基-10-(甲硫基)-5,6-二氢嘧啶并[5,4-e][1,2,4]三唑并[1,5-c]嘧啶(4l)的杀虫活性最高,死亡率达 95%。此外,8-(癸硫基)-2-((2,4-二氯苯氧基)甲基)-5-丙基-10-(甲硫基)-5,6-二氢嘧啶并[5,4-e][1,2,4]三唑并[1,5-c]嘧啶(4i)对苘麻(Abutilon theophrasti)表现出广谱的芽后除草活性、Amaranthus spinosus、Chenopodium album、Digitaria sanguinalis、Echinochloa crusgalli 和 Setaria viridis 的广谱除草活性,与阳性对照氟磺胺草醚相当。然而,所有合成的新化合物对四种植物病原真菌(包括灰霉病菌、疫霉病菌、Elsinoe fewcetti 和 Diaporthe medusaea)的杀菌活性都很弱。化合物 4l 具有显著的杀虫活性,化合物 4i 具有优异的除草活性,这两种化合物有望成为进一步研究的先导化合物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Design, synthesis, and biological activity of new 8-decylthio-10-methylthio-pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives

A series of new 8-decylthio-10-methylthio-pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives was prepared and characterized by FTIR, 1H NMR, 13C NMR, and HRMS. The bioassay results revealed that the title compounds had moderate to excellent insecticidal activities against Aphis fabae at a concentration of 500 mg/L. Among them, 8-(decylthio)-2-((4-chlorophenoxy)methyl)-5-propyl-10-(methylthio)-5,6-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine (4l) exhibited the highest insecticidal activity, with 95% mortality. Moreover, 8-(decylthio)-2-((2,4-dichlorophenoxy)methyl)-5-propyl-10-(methylthio)-5,6-dihydropyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine (4i) showed broad-spectrum postemergence herbicidal activities against Abutilon theophrasti, Amaranthus spinosus, Chenopodium album, Digitaria sanguinalis, Echinochloa crusgalli, and Setaria viridis, which were equivalent to the positive control flumetsulam. However, all new synthesized compounds displayed weak fungicidal activity against four kinds of phytopathogenic fungi including Botrytis cinerea, phytophythora capsici, Elsinoe fewcetti, and Diaporthe medusaea. Compound 4l with remarkable insecticidal activity, and compound 4i with excellent herbicidal activity could be promising lead compounds for further investigation.

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来源期刊
CiteScore
2.60
自引率
7.70%
发文量
103
审稿时长
2.1 months
期刊介绍: Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.
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